By: Lindsay Garbacik By: Lindsay Garbacik | April 22, 2022 | Lifestyle Feature Culture Community
Summer is on the horizon and so is Chicago’s packed lineup of summer festivals! We’ve compiled a list of the biggest and best festivals for music, food, arts, pride and airplanes in Chicago this summer. So whether you’re looking to try a new dish from a food truck, or have your eye on a live concert, there are literally festivals every weekend in Chicago this summer to get you out of your comfort zone and revel in the excitement of the city.
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1000 W Armitage Ave. / Website
Dates: Friday, May 20 - Sunday, May 22
Join the festival for its 25th anniversary celebration and sip on cold beer , enjoy tasty festival foods and explore the many stages of live music. Full music lineup to be announced.
A $15 donation is suggested and can be made at the gate. Cash only.
Multiple Locations / Website
Dates: Friday, May 13 - Friday, May 20
Support local breweries and indulge in a variety of unique Illinois brews at this weeklong affair. There will be craft beer events for guests both in-person events and at home.
Registration is required for each event and can be done here.
Division Street / Website
Dates: Friday, June 3 - Sunday, June 5
Enjoy three days of live music, expertly chosen by local venues The Empty Bottle and Subterranean, accompanied by food trucks, a fashion presentation and family-friendly events for kids.
A $10 donation is highly encouraged.
57th St. / Website
Date: Saturday, June 4
Browse through a variety of artists and creatives peddling quality fine art, fine crafts, glass, jewelry, leather, photography, printmaking, paintings, sculpture, digital art, wood, ceramics and more.
201 E Randolph St. / Website
Date: Saturday, June 4
Bring the whole family for a day of gospel music concerts and other live performers sure to brighten any day.
201 E Randolph St. / Website
Dates: Thursday, June 9 - Sunday, June 12
Experience the Chicago-born blues in real time at one of the many diverse blues performances in Millenium Park.
5217 N Clark St. / Website
Dates: Friday, June 10 - Sunday, June 12
Celebrate Swedish tradition with three days of street revelry, including: live music, unique vendors, food stands and activities for kids.
9501 Skokie Blvd. / Website
Dates: Tuesday, June 14 - Sunday, June 19
Celebrate the art of the flamenco dance with three days of concerts and four days of talks from industry professionals.
337 E Randolph St. / Website
Dates: Wednesday, June 15 - Saturday, Aug. 20
Enjoy live classical music gracefully performed by the Grant Park Orchestra and Chorus as you lounge on the grass and picnic with friends.
Halsted Street / Website
Dates: Saturday, June 18 - Sunday, June 19
Get a head start on Pride with this festival the weekend before Chicago’s Pride Parade. Explore three live music stages, food and drink vendors, drag shoes, pet parades, and over 150 vendors selling fine arts and crafts.
A $15 donation is highly encouraged.
Douglass Park / Website
Dates: Friday, June 17 - Sunday, June 19
Experience one of the biggest music festivals in the Midwest with Post Malone, Playboi Carti and Young Thug x Gunna headlining this year.
900 W Randolph St. / Website
Dates: Friday, June 17 - Sunday, June 19
Celebrating its 25th anniversary, join the fun with dishes from 16 of Chicago’s top restaurants, a stellar lineup of live music and DJs, and many exciting vendors.
4100 N Ravenswood Ave. / Website
Dates: Saturday, June 18 - Sunday, June 19
Try an array of craft beers and Chicago-native restaurants and food trucks at this two-day outdoor festival.
Navy Pier / Website
Dates: Saturday, June 18 - Sunday, June 19
Ten nationally ranked F50 catamarans teams will go head to head as the event makes its debut in Chicago for the very first time.
Millenium Park / Website
Dates: Mondays & Thursdays, June 20 - Aug. 18
Enjoy a variety of musical guests at Jay Pritzker Pavilion this summer.
4100 S Lake Shore Dr. / Website
Date: Saturday, June 25
Prepare your pink outfits for this insta-worthy, music-filled, rosé-soaked event.
2579 N Milwaukee Ave. / Website
Dates: Saturday, June 25 - Sunday, June 26
Raise money for neighborhood nonprofits while enjoying live music, art, food and drinks at this crowd-favorite festival.
Grant Park / Website
Dates: Friday, July 8 - Sunday, July 10
Try a bite of Chicago’s best dishes at this pop-up park celebration. There will be three live music stages and food from over 30 city eateries.
1800 W Chicago Ave. / Website
Dates: Friday, July 8 - Sunday, July 10
Bring your whole family (pets included) to this annual festival filled with street vendors, art stands. food trucks and live performances.
A $10 donation is suggested.
W Waveland Ave. & N Southport Ave./ Website
Dates: Saturday, July 9 - Sunday, July 10
Explore local artists selling everything from watercolor paintings, jewelry, glass, to mixed media at this acclaimed neighborhood street festival.
Union Park / Website
Dates: Friday, July 15 - Sunday, July 17
Enjoy three days filled with up-and-coming artists, specialty record vendors, unique poster stands and great offerings from the local food scene.
Single day General Admission tickets start at $99 while the 3-Day, General Admission pass is $200.
1425 N Damen Ave / Website
Dates: Friday, July 22 - Sunday, July 24
Celebrate the neighborhood and summer with live music, local food, art and retail vendors.
A donation of $10 is suggested. All proceeds benefit the local Wicker Park Bucktown Chamber of Commerce.
1340 W Washington Blvd (Plumbers Hall) / Website
Dates: Saturday, July 23 - Sunday, July 24
Try a variety of pizzas from the best pizzerias in the city. 39 pizza makers will set up shop in the West Loop for two days of live music, seminars, panel discussions, live demonstrations and lots of pizza.
General Admission 1-Day tickets start at $59 and 2-Day tickets at $89.
Grant Park/ Website
Dates: Thursday, July 28 - Sunday, July 31
Experience the best in music at one of Chicago's biggest music festivals. This year's headliners include Doja Cat, Metallica, Green Day, Dua Lipa, J. Cole, Machine Gun Kelly, and Glass Animals, to name a few. With nine stages and over 170 bands, there's something for everyone.
General Admission 1-Day tickets start at $125 and 4-day tickets start at $350. Visit their website for full details.
State Street / Website
Dates: Select Sundays July 24 - Sept. 4
Back by popular demand, enjoy Sunday block parties throughout the summer, complete with food, art, drinks and shopping.
1341 W Randolph St / Website
Dates: Saturday, July 30 - Sunday, July 31
Shop for vintage clothes, antique furniture and handmade creations at this huge festival. There will be over 200 vendors and the festival will span both indoors and outdoors.
See their website for ticket pricing and more information.
United Center / Website
Dates: Thursday, Aug. 4 - Sunday, Aug. 7
Mark your calendar for this popular country music festival. This year’s lineup includes Sam Hunt, Willie Nelson, Tim McGraw, Miranda Lambert and more, along with the best barbecue from the world’s top pitmasters.
Ticket prices range from $45 for a 1-Day Sunday General Admission ticket to $185 for a 4-Day pass.
1700 - 1800 W Hubbard St. / Website
Dates: Friday, Aug. 5 - Sunday, Aug. 7
Relive the days of the Grateful Dead and rock out to three days of jam bands, a large array of craft beer, and dancing in the streets.
523 S Webster St. / Website
Dates: Friday, Aug. 5 - Sunday, Aug. 7
Celebrate all things Italian at this Naperville event. There will be live music, a meatball eating contest, and a Tuscany-inspired wine bar.
Check out their website for information on ticket pricing.
Halsted Street / Website
Dates: Saturday, Aug. 6 - Sunday, Aug.
With six stages of live music, half a mile of festivities, and pride to spare, this festival is a must. Enjoy DJs, dancing, cocktails and more in the historic Northalsted neighborhood.
A $15 donation is highly suggested and goes towards community projects like the Chicago Pride crosswalks.
1600 N Lake Shore Dr. / Website
Dates: Saturday, Aug. 20 - Sunday, Aug. 21
Watch in awe at this free aerial show above Lake Michigan. The show can be seen along the lakefront.
Photography by: Josh Howard for Unsplash
